Biosynthetic Studies on Geldanamycin and Pactamycin

The formation of the m-C(,7)N units of geldanamycin and pactamycin via the shikimate pathway was studied. {('13)C(,6)}glucose was used to determine the incorporation of intact carbon units into both molecules. This revealed that the respective m-C(,7)N units were derived from three-carbon and four-carbon subunits (specifically phosphoenol pyruvate and erythrose-4-phosphate). In the case of geldanamycin C-15, C-16 and C-21 originated from the C(,3) unit and C-17 through C-20 from the C(,4) unit. This pattern was obtained by analysis of coupling patterns and coupling constants in the ('13)C NMR spectrum as well as homonuclear ('13)C-('13)C decoupling. Similarly, in the case of pactamycin C-2'' through C-5'' were derived from the C(,4) unit and C-1'', C-6'' and C-7'' from the C(,3) unit. The ('13)C NMR spectra of geldanamycin and pactamycin labeled by {('13)C(,6)}-glucose were analysed in terms of the incorporation of intact subunits into the rest of the molecules.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

1983

Author dc:creator

• Potgieter, Maria

• Chemistry, Organic

Identifier

(UMI)AAI8410026

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70248